dihydrogenistein

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: dihydrogenistein
• 英文别名: DHG；3-(4-hydroxyphenyl)-2H-chromene-4,5,7-triol
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: UUXZIKHMKXXLGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dihydrogenistein 、 N,O-双(三甲基硅烷基)三氟乙酰胺 反应 0.08h， 生成 Dihydrogenistein (enol), TMS
  参考文献：
  名称：

  Biosynthesis of (−)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion

  摘要：

  Equols are isoflavandiols formed by reduction of soy isoflavones such as daidzein and genistein by gut microorganisms. These phytoestrogens are of interest for their various biological effects. We report biosynthesis from genistein to (-)-5-hydroxy-equol in recombinant E. coli expressing three reductases (daidzein reductase DZNR, dihidroclaidzein reductaier DHDR, tetrahydrodaidzein reductase THDR) and a racemase (dihydrodaidzein racemase, DDRC) originating from the Or, bacterium, Slackia isoflavoniconvertens. The biosynthesized 5-hydroxy4equol proved as an optically negative enantioiner,, none-theless it displayed an inverse Circular dichroism spectrum to (S)-equol. Compartmentalized expression of DZNR and DDRC in one E. coli strain and DHDR and THDR in another increased the yield, to 230 mg/L and the productivity to 38 mg/L/h. If the last reductase was Missing, the intermediate spontaneously dehydrated to 5-hydroxy-dehydroequol in up to 99 mg/L This novel isoflavene, previously not known to be synthesized in nature, was also detected in this biotransformation system:, Although (S)-equol favors binding to human estrogen receptor (hER) beta over,hER alpha, (-)-5-hydroxy-equol showed the opposite preference. This study provides elucidation of the biosynthetic route of (-)-5-hydroxy-equol and measurement of its potent antagonistic character as a phytoestrogen for the first time.

  DOI：

  10.1021/acschembio.7b00624
• 作为产物：
  描述：

  染料木素 在 葡萄糖 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 甘油 为溶剂， 反应 3.0h， 生成 dihydrogenistein
  参考文献：
  名称：

  Biosynthesis of (−)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion

  摘要：

  Equols are isoflavandiols formed by reduction of soy isoflavones such as daidzein and genistein by gut microorganisms. These phytoestrogens are of interest for their various biological effects. We report biosynthesis from genistein to (-)-5-hydroxy-equol in recombinant E. coli expressing three reductases (daidzein reductase DZNR, dihidroclaidzein reductaier DHDR, tetrahydrodaidzein reductase THDR) and a racemase (dihydrodaidzein racemase, DDRC) originating from the Or, bacterium, Slackia isoflavoniconvertens. The biosynthesized 5-hydroxy4equol proved as an optically negative enantioiner,, none-theless it displayed an inverse Circular dichroism spectrum to (S)-equol. Compartmentalized expression of DZNR and DDRC in one E. coli strain and DHDR and THDR in another increased the yield, to 230 mg/L and the productivity to 38 mg/L/h. If the last reductase was Missing, the intermediate spontaneously dehydrated to 5-hydroxy-dehydroequol in up to 99 mg/L This novel isoflavene, previously not known to be synthesized in nature, was also detected in this biotransformation system:, Although (S)-equol favors binding to human estrogen receptor (hER) beta over,hER alpha, (-)-5-hydroxy-equol showed the opposite preference. This study provides elucidation of the biosynthetic route of (-)-5-hydroxy-equol and measurement of its potent antagonistic character as a phytoestrogen for the first time.

  DOI：

  10.1021/acschembio.7b00624

文献信息

• THERAPEUTIC METHODS AND COMPOSITIONS INVOLVING ISOFLAVONES
  申请人：KELLY Graham Edmund

  公开号：US20080287528A1

  公开（公告）日：2008-11-20

  Therapeutic methods of treatment, compositions and foodstuffs are described which contain isoflavone compounds described by general formula (1), in which Z is H, R 1 is H, or R A CO where R A is C 1-10 alkyl or an amino acid, R 2 is H, OH, or OR B where R B is an amino acid, or COR A where R A is as previously defined, W is H, A is H or OH, and B is selected from (a), (b), (c), or W is H, and A and B taken together form a six-membered ring selected from (d), or W, A and B taken with the groups with which they are associated comprise (e), or W and A taken together with the groups with which they are associated comprise (f) and B is (g) wherein R 3 is H, COR A where R A is as previously defined, CO 2 R C where R C is C 1-10 alkyl, or COR B where R B is as previously defined, R 4 is H, COR D where R D is H, OH, C 1-10 alkyl or an amino acid, CO 2 R C where R C is as previously defined, COR E where R E is H, C 1-10 alkyl or an amino acid, COOH, COR C where R C is as previously defined, or CONHR E where R E is as previously defined, R 5 is H, CO 2 R C where R C is as previously defined, or COR C OR E where R C and R E are as previously defined, and where the two R 5 groups are attached to the same group they are the same or different, R 6 is H or hydroxy C 1-10 alkyl, X is preferably O, but may be N or S, and Y is (h) where R 7 is H, or C 1-10 alkyl.

  本文描述了治疗方法、组合物和食品，其中包含一般式（1）所描述的异黄酮化合物，其中Z为H，R1为H或RACO，其中RA为C1-10烷基或氨基酸，R2为H、OH或ORB，其中RB为氨基酸，或CORA，其中RA如先前定义，W为H，A为H或OH，B选自（a）、（b）、（c），或W为H，A和B结合形成六元环，选自（d），或W、A和B与它们相关的基团组成（e），或W和A与它们相关的基团组成（f），B为（g），其中R3为H，CORA，其中RA如先前定义，CO2RC，其中RC为C1-10烷基，或CORB，其中RB如先前定义，R4为H，CORD，其中RD为H、OH、C1-10烷基或氨基酸，或CO2RC，其中RC如先前定义，CORE，其中RE为H、C1-10烷基或氨基酸，或COOH，CORC，其中RC如先前定义，或CONHRE，其中RE如先前定义，R5为H，CO2RC，其中RC如先前定义，或CORCORE，其中RC和RE如先前定义，且当两个R5基团连接到同一基团时，它们相同或不同，R6为H或羟基C1-10烷基，X优选为O，但也可以为N或S，Y为（h），其中R7为H或C1-10烷基。
• IMPROVEMENTS IN CANCER TREATMENT WITH ISOFLAVONOIDS
  申请人：Noxopharm Limited

  公开号：EP3939583A1

  公开（公告）日：2022-01-19

  The invention relates to a composition including an oleaginous base for use in a device for rectal, vaginal or urethral application and a compound of general formula (I), particularly an isoflavonoid, for improving the bioavailability of the latter, as well as its use in cancer therapy.

  本发明涉及一种组合物，该组合物包括用于直肠、阴道或尿道施用装置的含油基质和通式（I）化合物，特别是异黄酮类化合物，用于提高后者的生物利用度，以及在癌症治疗中的应用。
• Radiotherapy improvements
  申请人：NOXOPHARM LIMITED

  公开号：US11229703B2

  公开（公告）日：2022-01-25

  A method for inducing abscopal, complete or partial response to radiotherapy comprising administering isoflavone compounds and irradiating with a cytotoxic dose of ionising radiation so that fewer than all of the plurality of tumours are irradiated.

  一种诱导对放疗的缺席反应、完全反应或部分反应的方法，包括施用异黄酮化合物，并用细胞毒性剂量的电离辐射照射，使受到照射的多个肿瘤少于全部肿瘤。
• ISOFLAVONOID COMPOSITION WITH IMPROVED PHARMACOKINETICS
  申请人：NOXOPHARM LIMITED

  公开号：US20190117618A1

  公开（公告）日：2019-04-25

  A method for providing a steady state plasma concentration of about 20-400 ng/ml of isoflavonoid compounds comprising the steps of a first rectal administration of the compound in a lipophilic suppository base followed by further rectal administrations no earlier than 4, 8 or 16 hours after the previous rectal administration.
• CHEMOTHERAPY IMPROVEMENTS
  申请人：NOXOPHARM LIMITED

  公开号：US20190117620A1

  公开（公告）日：2019-04-25

  A method for treating or preventing cancer including administering to a person in need thereof a first composition including a platin, a taxane, or combination of same and a second composition including an isoflavonoid.